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Synthesis of Heterofunctional Polyester Dendrimers with Internal and External Functionalities as Versatile Multipurpose Platforms
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.ORCID iD: 0000-0001-6112-0450
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.ORCID iD: 0000-0001-8464-461X
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology, Coating Technology.
KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Fibre- and Polymer Technology.ORCID iD: 0000-0002-9597-9578
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2020 (English)In: Biomacromolecules, ISSN 1525-7797, E-ISSN 1526-4602, Vol. 21, no 10, p. 4273-4279Article in journal (Refereed) Published
Abstract [en]

Heterofunctional dendrimers with internal and external representations of functionalities are considered as the ultimate dendritic frameworks. This is reflected by their unprecedented scaffolding, such as precise control over the structure, molecular weight, number, and location of different cargos across the whole dendritic skeleton. Consequently, these dendrimers with multipurpose characters are the pinnacle of precision polymers and thereof are highly attractive to the scientific community as they can find use in a great number of cutting-edge applications, especially as discrete unimolecular carriers for therapeutic exploitation. Unfortunately, most established dendrimer families display external functionalities but lack internal scaffolding ability, which leads to inherent limitations to their full potential use as precision carriers. Consequently, here, we embark on a novel synthetic strategy facilitating the introduction of internal functionalization of established dendrimers. As a proof of concept, a new class of internally and externally functionalized multipurpose dendrimers based on the established 2,2-bis(methylol)propionic acid (bis-MPA) was successfully obtained by the elegant and simple design of AB2C monomers, amalgamated from two traditional AB2 monomers. Utilizing fluoride-promoted esterification (FPE), straightforward layer-by-layer divergent growth up to the fourth generation was successful in less than one day of reaction time, with a molecular weight of 15 kDa, and displaying 93 reactive groups divided by 45 internal and 48 external functionalities. The feasibility of postfunctionalization through click reactions is demonstrated, where the fast and effective attachment of drugs, dyes, and PEG chains is achieved, as well as cross-linking into multifunctional hydrogels. The simplicity and versatility of the presented strategy can easily be transferred to generate a myriad of functional materials such as polymers, surfaces, nanoparticles, or biomolecules.

Place, publisher, year, edition, pages
American Chemical Society (ACS) , 2020. Vol. 21, no 10, p. 4273-4279
National Category
Polymer Technologies
Identifiers
URN: urn:nbn:se:kth:diva-288023DOI: 10.1021/acs.biomac.0c01068ISI: 000580890000030PubMedID: 32852953Scopus ID: 2-s2.0-85090825509OAI: oai:DiVA.org:kth-288023DiVA, id: diva2:1512546
Note

QC 20201223

Available from: 2020-12-23 Created: 2020-12-23 Last updated: 2022-06-25Bibliographically approved

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Garcia-Gallego, SandraStenström, PatrikAntunez, Pablo MesaZhang, YuningMalkoch, Michael

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Garcia-Gallego, SandraStenström, PatrikAntunez, Pablo MesaZhang, YuningMalkoch, Michael
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